This thesis explores ways in which the outsider questions rather than confirms dominant cultural values whilst avoiding the crudity of overt politicisation. I argue that the outsider's preference for an observer's stance is not so much an act which denies responsibility to the world of his day, but rather a means of reassessing its priorities. In Section One, I discuss Conrad's role as an outsider in the age of Empires. I demonstrate the ways in which Conrad employs narrators, frequently using strategies of irony which can be and have been read in very different ways. I argue that Conrad uses irony as a tool for condemnation rather than condonement of imperialist practice, if not its ideology. In Section Two, I discuss Lowry as an emigre from England (so contrasting him with Conrad, the immigrant from Europe), and examine his dissenting voice which opposes bourgeois prejudice against the working class, a totalising ideology like Fascism, and a Western rationalism which sees too rigid a distinction between sanity and madness. I demonstrate how Lowry as an outsider reacts to the age of twentieth century World Wars. In Section Three, I discuss Naipaul's role as an outsider in the age of decolonisation, when bogus liberals and false redeemers fail to rebuild the newly independent post-colonial states. As in Conrad's case, I show how a failure to read Naipaul's ironic tone of voice has given rise to radically divergent views as to what he is about. I also link Conrad and Naipaul through their cultural negotiation between the 'centre' and its peripheries. By looking at these three writers in chronological order and offering a comparative perspective on their work, I highlight the outsider's disturbing, yet illuminating role within a historical context. I also draw attention to creative tensions between artistic concerns and a serious political purpose. I assess the outsider as observer and man of conscience rather than as a` mere onlooker. I conclude that the outsider also fulfils a social obligation by promoting critical awareness on the reader's side by means of his defamiliarising perspective.